Find Hotels with Bars in Pittsfield, MA

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Hotels with Bars

Top Pittsfield Hotels with Bars

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (860)
"Consistently a clean room with welcoming staff."
The price is NT$3,450
NT$3,853 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (639)
"It’s a three star hotel charging 5 star prices. They should include free breakfast."
The price is NT$4,527
NT$5,057 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Lenox Pittsfield

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (755)
"Staff were excellent and welcoming."
Hotel On North

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (407)
"Very comfortable room that worked great for our family. "
The price is NT$5,329
NT$6,622 total
includes taxes & fees
Sep 15 - Sep 16
The Porches Inn at Mass MoCA

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (693)
"Pleasant stay"
The price is NT$2,745
NT$3,485 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1005)
"Wonderful place to stay"
The price is NT$4,022
NT$4,493 total
includes taxes & fees
Sep 8 - Sep 9
The Yankee, Trademark Collection by Wyndham

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (680)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is NT$4,796
NT$5,357 total
includes taxes & fees
Aug 18 - Aug 19
Berkshires Untold

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (569)
"Fabulous place"
The price is NT$4,559
NT$5,093 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Lenox Berkshires

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is NT$4,559
NT$5,093 total
includes taxes & fees
Sep 1 - Sep 2
Element Lenox Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is NT$3,830
NT$5,451 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Pittsfield Hotel Reviews

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 74 hotels and other lodging options to choose from, and likely many will have a bar where you can enjoy a beer after a day out and about exploring. While you're here, consider a visit to Berkshire Museum and Colonial Theater.
What are the best hotels with bars in Pittsfield?
Here's some of the top Pittsfield accommodations with bars: Holiday Inn & Suites Pittsfield-Berkshires by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hilton Garden Inn Lenox Pittsfield: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hotel On North: Enjoy the bar, free WiFi, and free parking.
How many hotels with onsite bars should I expect to find in Pittsfield?
Expedia has 8 hotels with a bar in Pittsfield.
What is there to do in Pittsfield?
If you have time to explore, consider visiting Berkshire Museum, Colonial Theater, and Barrington Stage Company, and then find a cozy spot for a nightcap. Other places to see include Bousquet Ski Area and Hancock Shaker Village. Pittsfield is appreciated for its entertainment venues.
When is the best time to visit Pittsfield?
Visiting local bars in Pittsfield is more fun when you know what the weather holds. These temperatures and rainfall averages can help you determine the best time for bar hopping. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Pittsfield and around the area?
You might want to make the most of these transportation choices in and around Pittsfield: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.